WO2018102503A1 - Composition for remediating iron sulfide in oilfield production systems - Google Patents
Composition for remediating iron sulfide in oilfield production systems Download PDFInfo
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- WO2018102503A1 WO2018102503A1 PCT/US2017/063860 US2017063860W WO2018102503A1 WO 2018102503 A1 WO2018102503 A1 WO 2018102503A1 US 2017063860 W US2017063860 W US 2017063860W WO 2018102503 A1 WO2018102503 A1 WO 2018102503A1
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- 0 *C1N(*)C(*)=NC1* Chemical compound *C1N(*)C(*)=NC1* 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
- C09K8/524—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning organic depositions, e.g. paraffins or asphaltenes
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
- C09K8/528—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning inorganic depositions, e.g. sulfates or carbonates
- C09K8/532—Sulfur
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/04—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in markedly acid liquids
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- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/12—Oxygen-containing compounds
- C23F11/124—Carboxylic acids
- C23F11/126—Aliphatic acids
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/16—Sulfur-containing compounds
- C23F11/161—Mercaptans
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- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
- C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
- C23G1/061—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors nitrogen-containing compounds
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- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
- C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
- C23G1/065—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors sulfur-containing compounds
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- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/08—Iron or steel
- C23G1/088—Iron or steel solutions containing organic acids
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- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/32—Anticorrosion additives
Definitions
- compositions are provided, and more particularly compositions for removing oilfield hydrocarbon and iron sulfide based deposits from equipment and for providing protection to the equipment against corrosive fluids and gases.
- This form of deposit is referred to in the industry as schmoo. If left untreated, this form of deposition can plug lines, which can lead to loss of revenue and/or equipment failure, and further, can result in casualties. Due to lines which cannot be mechanically cleaned, a chemical solution is needed that can be injected into the system to maintain control of the deposition in the lines.
- Corrosion inhibitors work primarily by forming protective films on the surfaces of the infrastructure. This creates a protective barrier from the corrosive fluids. If the schmoo deposition described above is present on the internal surfaces, it does not allow the dosed corrosion inhibitor to effectively coat and protect the equipment.
- the composition comprises an iron sulfide dissolver, an organic solvent, and a corrosion inhibitor.
- the iron sulfide dissolver comprises allaric acid, altaric acid, altraric acid, altronic acid, arabinaric acid, arabinonic acid, dihomocitric acid, fructuronic acid, fuconic acid,galactaric acid, galactonic acid, galacturonic acid, glucaric acid, glucoheptonic acid, gluconic acid, glucuronic acid, gulonic acid, homocitric acid, homoisocitric acid, idaric acid, idonic acid, iduronic acid, isocitric acid, mannaric acid, mannonic acid, octulosonic acid, rhamnonic acid, ribonic acid, tagaturonic acid, xylonic acid, or xyluronic acid, or a salt or derivative thereof, or
- the iron sulfide dissolver comprises gluconic acid or a salt thereof, glucaric acid or a salt or derivative thereof, or a combination thereof. More preferably, the iron sulfide dissolver comprises sodium gluconate, ammonium gluconate, potassium gluconate, lithium gluconate, magnesium gluconate, calcium gluconate, cesium gluconate, gluconic acid, sodium glucarate, ammonium glucarate, potassium glucarate, lithium glucarate, magnesium glucarate, calcium glucarate, cesium glucarate, glucaric acid, or a combination thereof.
- Derivatives of the acids described above can be, for example, aldehydo, dehydro, deoxy, erthyro, keto, lower alkyl (e.g., methyl, ethyl, propyl), oxo, or threo forms of the acid or its salt.
- the organic solvent comprises an alcohol, a hydrocarbon, a ketone, an ether, an alkylene glycol, a glycol ether, an amide, a nitrile, a sulfoxide, an ester, a polyol, or a combination thereof.
- the organic solvent can comprise methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, methylene glycol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, diethyleneglycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel, toluene, xylene, heavy aromatic naphtha, cyclohexanone, diisobutylketone, diethyl ether, propylene carbonate, N-methylpyrrolidinone, N,N-dimethylformamide
- composition can comprise water as an additional solvent.
- the corrosion inhibitor can comprise an imidazoline compound, a quaternary ammonium compound, a pyridinium compound, or a combination thereof.
- the corrosion inhibitor comprises one or more of the following imidazoline compounds:
- R 10 is a C1-C20 alkyl or a C1 -C20 alkoxyalkyl group
- R 12 and R 13 are independently hydrogen or a C1-C6 alkyl group
- R 11 and R 14 are independently hydrogen, C 1 -C6 alkyl, C 1 -C6 hydroxyalkyi, or C6 arylalkyl
- X " is a halide, carbonate, sulfonate, phosphate, or an anion of an organic carboxylic acid
- R 10 is a C 1 -C 2 0 alkyl or a C 1 -C 2 0 alkoxyalkyl group
- R 12 and R 13 are independently hydrogen or a CrC 6 alkyl group
- R 11 and R 14 are independently hydrogen, C 1 -C6 alkyl, C 1 -C6 hydroxyalkyi, or C6 arylalkyl;
- X " is a halide, carbonate, sulfonate, phosphate, or an anion of an organic carboxylic acid
- Ri and R 2 are each independently unsubstituted branched, chain or ring alkyl or alkenyl having from 1 to about 29 carbon atoms; partially or fully oxygenized, sulfurized, and/or phosphorylized branched, chain, or ring alkyl or alkenyl having from 1 to about 29 carbon atoms; or a combination thereof;
- R 3 and R 4 are each independently unsubstituted branched, chain or ring alkylene or alkenylene having from 1 to about 29 carbon atoms; partially or fully oxygenized, sulfurized, and/or phosphorylized branched, chain, or ring alkylene or alkenylene having from 1 to about 29 carbon atoms; or a combination thereof;
- l_i and L 2 are each independently absent, H, -COOH, -SO3H, -PO3H2,
- R 5 is each independently a branched or unbranched alkyl, aryl, alkylaryl, alkylheteroaryl, cycloalkyi, or heteroaryl group having from 1 to about 10 carbon atoms; n is 0 or 1 , and when n is 0, L 2 is absent or H;
- x is from 1 to about 10;
- y is from 1 to about 5;
- the corrosion inhibitor comprises a quaternary ammonium compound of Formula (IV):
- R-i, R 2 , and R 3 are independently Ci to C 20 alkyl, R 4 is methyl or benzyl, and X " is a halide or methosulfate.
- the corrosion inhibitor does not include a phosphate ester.
- the method comprises adding an iron sulfide dissolver to a fluid which contacts a surface of a wellbore or equipment used in production, processing, transportation, storage or separation of the fluid to inhibit corrosion and/or remove hydrocarbonaceous deposits from the surface.
- the iron sulfide dissolver comprises sodium gluconate, ammonium gluconate, potassium gluconate, lithium gluconate, magnesium gluconate, calcium gluconate, cesium gluconate, gluconic acid, sodium glucarate, ammonium glucarate, potassium glucarate, lithium glucarate, magnesium glucarate, calcium glucarate, cesium glucarate, glucaric acid, or a combination thereof.
- the fluid comprises natural gas or a liquid hydrocarbon.
- hydrocarbonaceous deposits from a surface is provided.
- the method comprises adding the composition as described above to a fluid which contacts a surface of a wellbore or equipment used in production, processing, transportation, storage or separation of the fluid to inhibit corrosion and/or remove hydrocarbonaceous deposits from the surface.
- the fluid comprises natural gas or a liquid hydrocarbon.
- the equipment comprises a pipeline, a storage vessel, downhole injection tubing, a flow line, or an injection line.
- the liquid hydrocarbon comprises crude oil, heavy oil, processed residual oil, bituminous oil, coker oil, gas oil, fluid catalytic cracker feed or slurry, naphtha, diesel fuel, fuel oil, jet fuel, gasoline, or kerosene.
- Figure 1 is a graph of the corrosion rate versus time in a bubble test and shows corrosivity of sodium gluconate (-+- 37,000 ppm; -X- 10,000 ppm, and -o- 1 ,000 ppm) )as compared to THPS (-A- 37,000 ppm; - ⁇ - 10,000 ppm, and
- Figure 2 is a graph of the corrosion rate versus time in a bubble test to show the effect of a sodium gluconate formulation (-e-)on corrosion performance as compared to an incumbent material containing THPS (-A-);
- Figure 3 is a graph of the concentration of solubilized iron versus total treatment (wt. % iron sulfide dissolver) in an iron sulfide solubilization test to show the effect of a corrosion inhibitor including 25% sodium gluconate (- ⁇ -) in dissolving iron sulfide as compared to the same material including 25% THPS (-A-); corrosion inhibitor control (- ⁇ -).
- compositions are useful in crude oil based and natural gas based products, processes, and refinery streams.
- the described compositions are particularly effective for inhibiting corrosion of mild steel in hydrocarbon, oil/brine mixtures, and aqueous systems.
- compositions are also particularly useful for removing hydrocarbonaceous deposits (e.g., schmoo) from metallic or mineral surfaces in contact with a fluid in oil and gas applications, including removal of iron sulfide to reduce the risk of corrosion failures due to under deposit corrosion.
- the compositions can be used in sweet systems (i.e., systems having a relatively high carbon dioxide concentration) or in systems having sour conditions (i.e., relatively high hydrogen sulfide concentration).
- sweet systems i.e., systems having a relatively high carbon dioxide concentration
- sour conditions i.e., relatively high hydrogen sulfide concentration
- the compositions are useful in a wide range of climates and under a wide range of process conditions, (e.g., 0°C to 200°C), where other available cleaner/corrosion inhibitor compositions fail.
- compositions comprise an iron sulfide dissolver comprising allaric acid, altaric acid, altraric acid, altronic acid, arabinaric acid, arabinonic acid, dihomocitric acid, fructuronic acid, fuconic acid,galactaric acid, galactonic acid, galacturonic acid, glucaric acid, glucoheptonic acid, gluconic acid, glucuronic acid, gulonic acid, homocitric acid, homoisocitric acid, idaric acid, idonic acid, iduronic acid, isocitric acid, mannaric acid, mannonic acid, octulosonic acid, rhamnonic acid, ribonic acid, tagaturonic acid, xylonic acid, or xyluronic acid, or a salt of any of these acids or a derivative of any of these acids or their salts, or a combination thereof, preferably gluconic acid or a salt thereof, glucaric acid or a salt thereof, glucar
- the iron sulfide dissolver can either inhibit the formation of iron sulfide or dissolve iron sulfide.
- suitable salts of the iron sulfide dissolver include alkali metal or alkaline earth metal salts, such as sodium, potassium, lithium, magnesium, calcium or cesium salts.
- the unexpected, superior cleaning performance of the disclosed compositions results from dissolution of iron sulfide at treated surfaces (e.g., interior of pipeline, dirty production equipment).
- the iron sulfide dissolver in addition to cleaning performance, can act as a corrosion inhibitor, and is more compatible with steel piping and equipment such as mild steel that existing iron sulfide dispersants used in oilfield applications.
- compositions can provide both corrosion protection and a cleaning effect for applications relating to the production, transportation, storage, and separation of crude oil and natural gas.
- the compositions can improve production in an oil and/or gas application by reducing a corrosion rate of and/or removing
- hydrocarbonaceous deposits e.g., schmoo
- the compositions can enhance oil and gas production by keeping surface facility equipment, pipelines, downhole injection tubing and infrastructure, and pore throats around an injector clean to accept an optimum water volume.
- the compositions can be used in continuous and/or batch dosages to clean out process equipment that has a tendency to accumulate deposits.
- compositions can provide greater than or equal to 90, 95, 96, 97, 98, 99 or 100% corrosion protection.
- the compositions can provide at least 98% corrosion protection after 12 hours, at least 98% corrosion protection after 18 hours, and/or at least 98% corrosion protection after 20 hours for a carbon steel working electrode in a bubble test, wherein the bubble test is characterized by a testing temperature of about 80 °C; a carbon dioxide saturated liquid medium of 10% field crude oil and 90% synthetic brine; and an inhibitor dosage of 10 ppm based on total fluids.
- compositions disclosed herein can include a corrosion inhibitor component comprised of one or more corrosion inhibitors.
- the corrosion inhibitor(s) can be present in an amount of about 5 wt. % to about 95 wt. %, about 10 wt. % to about 50 wt. %, or about 15 wt. % to about 30 wt. %, based on total weight of the composition.
- the corrosion inhibitor(s) can constitute about 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90 or 95 wt. % of the cleaner/corrosion inhibitor composition, based on total weight of the composition.
- the compositions comprise about 20 to about 30 wt. % of the corrosion inhibitor(s), based on total weight of the composition.
- Suitable corrosion inhibitors include, but are not limited to, alkyl, hydroxyalkyl, alkylaryl, arylalkyl or arylamine quaternary salts; mono or polycyclic aromatic amine salts; imidazoline derivatives; mono-, di-or trialkyl or alkylaryl phosphate esters; phosphate esters of hydroxy lam ines; phosphate esters of polyols; and monomeric or oligomeric fatty acids.
- the corrosion inhibitor component can comprise an imidazoline.
- the imidazoline can be, for example, imidazoline derived from a diamine, such as ethylene diamine (EDA), diethylene triamine (DETA), triethylene tetraamine (TETA) etc. and a long chain fatty acid such as tall oil fatty acid (TOFA).
- the imidazoline can be an imidazoline of Formula (I) or an imidazoline derivative.
- Representative imidazoline derivatives include an imidazolinium compound of Formula (II) or a bis-quaternized compound of Formula (III). Suitable imidazolines include those of Formula (I):
- R 10 is a C1 -C20 alkyl or a C1 -C20 alkoxyalkyl group
- R 11 is hydrogen, Ci -C 6 alkyl, C-I -C6 hydroxyalkyl, or C1 -C6 arylalkyl
- R 12 and R 13 are independently hydrogen or a C-I -C6 alkyl group.
- the imidazoline includes an R 10 which is the alkyl mixture typical in tall oil fatty acid (TOFA), and R 11 , R 12 and R 13 are each hydrogen.
- the corrosion inhibitor component can include an imidazolinium
- R 10 is a C1 -C20 alkyl or a C1 -C20 alkoxyalkyl group; R 11 and R 14 are
- the imidazolinium compound includes 1 - benzyl-1 -(2-hydroxyethyl)-2-tall-oil-2-imidazolinium chloride.
- the corrosion inhibitor can comprise a bis-quaternized compound having the formula (III):
- Ri and R 2 are each independently unsubstituted branched, chain or ring alkyl or alkenyl having from 1 to about 29 carbon atoms; partially or fully oxygenized, sulfurized, and/or phosphorylized branched, chain, or ring alkyl or alkenyl having from 1 to about 29 carbon atoms; or a combination thereof;
- R 3 and R 4 are each independently unsubstituted branched, chain or ring alkylene or alkenylene having from 1 to about 29 carbon atoms; partially or fully oxygenized, sulfurized, and/or phosphorylized branched, chain, or ring alkylene or alkenylene having from 1 to about 29 carbon atoms; or a combination thereof; and l_2 are each independently absent, H, -COOH, -S0 3 H, -P0 3 H 2 , -COOR5, - CONH2, -CONHR5, or -CON(R 5 ) 2 ;
- R 5 is each independently a branched or unbranched alkyl, aryl, alkylaryl, alkylheteroaryl, cycloalkyi, or heteroaryl group having from 1 to about 10 carbon atoms; n is 0 or 1 , and when n is 0, L 2 is absent or H;
- x is from 1 to about 10;
- y is from 1 to about 5.
- Ri and R 2 are each independently C6-C22 alkyl, C8-C20 alkyl, C12-C18 alkyl, C16-C18 alkyl, or a combination thereof;
- R 3 and R 4 are C1-C10 alkylene, C2- Cs alkylene, C2-C6 alkylene, or C2-C3 alkylene;
- n is 0 or 1 ;
- x is 2;
- y is 1 ;
- R 3 and R 4 are - C2H2-;
- U is -COOH, -SO3H, or -PO 3 H 2 ;
- L 2 is absent, H, -COOH, -SO3H, or - PO3H2.
- Ri and R 2 can be derived from a mixture of tall oil fatty acids and are predominantly a mixture of C17H33 and C17H31 or can be C16-C18 alkyl;
- R 3 and R 4 can be C2-C3 alkylene such as -C2H2-;
- n is 1 and L 2 is -COOH or n is 0 and L 2 is absent or H;
- x is 2;
- y is 1 ;
- R 3 and R 4 are -C2H2-; and
- l_i is -COOH.
- the corrosion inhibitor can comprise a bis-quaternized imidazoline compound having the formula (III) wherein R-i and R 2 are each independently C 6 -C 2 2 alkyl, C8-C20 alkyl, C12-C18 alkyl, or C16-C18 alkyl or a combination thereof; R 4 is C1-C10 alkylene, C2-C8 alkylene, C2-C6 alkylene, or C2-C3 alkylene; x is 2; y is 1 ; n is 0; l_i is- COOH, -SO3H, or -PO3H2; and L 2 is absent or H.
- a bis-quaternized compound has the formula (III) wherein R-i and R 2 are each independently Ci 6 -Ci 8 alkyl; R 4 is -C 2 H 2 -; x is 2; y is 1 ; n is 0; Li is-COOH, -SO3H, or -PO 3 H 2 and L 2 is absent or H.
- the imidazoline and/or imidazolinium compound can comprise 0 to 100 wt. %, about 10 to 60 wt. %, or about 30 to 45 wt. % of the corrosion inhibitor
- the imidazoline and/or imidazolinium compound can constitute about 30 to 40 wt. % of the corrosion inhibitor component, based on total weight of the corrosion inhibitor component.
- the corrosion inhibitor can be a quaternary ammonium compound of Formula (IV):
- R-i , R 2 , and R 3 are independently Ci to C20 alkyl, R 4 is methyl or benzyl, and X " is a halide or methosulfate.
- Suitable alkyl, hydroxyalkyl, alkylaryl, arylalkyi or aryl amine quaternary salts include those alkylaryl, arylalkyi and aryl amine quaternary salts of the formula [N + R 5a R 6a R 7a R 8a ][X ⁇ ] wherein R 5a , R 6a , R 7a , and R 8a contain one to 18 carbon atoms, and X is CI, Br or I.
- R 5a , R 6a , R 7a , and R 8a can each be independently selected from the group consisting of alkyl (e.g., Ci-Ci 8 alkyl),
- the mono or polycyclic aromatic amine salt with an alkyl or alkylaryl halide include salts of the formula [N + R 5a R 6a R 7a R 8a ][X ⁇ ] wherein R 5a , R 6a , R 7a , and R 8a contain one to 18 carbon atoms and at least one aryl group, and X is CI, Br or I.
- Suitable quaternary ammonium salts include, but are not limited to, a tetramethyl ammonium salt, a tetraethyl ammonium salt, a tetrapropyl ammonium salt, a tetrabutyl ammonium salt, a tetrahexyl ammonium salt, a tetraoctyl ammonium salt, a benzyltrimethyl ammonium salt, a benzyltriethyl ammonium salt, a phenyltrimethyl ammonium salt, a phenyltriethyl ammonium salt, a cetyl benzyldimethyl ammonium salt, a hexadecyl trimethyl ammonium salt, a dimethyl alkyl benzyl quaternary ammonium salt, a monomethyl dialkyl benzyl quaternary ammonium salt, or a trialkyi benzyl quaternary ammonium
- the quaternary ammonium salts can comprise 0 to 100 wt. %, about 20 to 80 wt. %, or about 50 to 65 wt.% of the corrosion inhibitor component, based on total weight of the corrosion inhibitor component.
- the quaternary ammonium salt constitutes about 50-60 wt.% of the corrosion inhibitor component, based on total weight of the corrosion inhibitor component.
- the corrosion inhibitor component can comprise a pyridinium salt such as those represented by Formula (V):
- R 9 is an alkyl group, an aryl group, or an arylalkyl group, wherein said alkyl groups have from 1 to about 18 carbon atoms and X " is a halide such as chloride, bromide, or iodide.
- X " is a halide such as chloride, bromide, or iodide.
- alkyl pyridinium salts and alkyl pyridinium benzyl quats.
- Exemplary compounds include methyl pyridinium chloride, ethyl pyridinium chloride, propyl pyridinium chloride, butyl pyridinium chloride, octyl pyridinium chloride, decyl pyridinium chloride, lauryl pyridinium chloride, cetyl pyridinium chloride, benzyl pyridinium chloride and an alkyl benzyl pyridinium chloride, preferably wherein the alkyl is a C1 -C6 hydrocarbyl group.
- the pyridinium compound includes benzyl pyridinium chloride.
- the pyridinium salt can constitute 0 wt. % to 100 wt. %, about 10 to 60 wt. %, or about 30 to 40 wt.% of the corrosion inhibitor component, based on total weight of the corrosion inhibitor component.
- the corrosion inhibitor components can include additional corrosion inhibitors such as phosphate esters, monomeric or oligomeric fatty acids, or alkoxylated amines. [0043]The corrosion inhibitor component can comprise a phosphate ester.
- Suitable mono-, di- and tri-alkyl as well as alkylaryl phosphate esters and phosphate esters of mono, di, and triethanolamine typically contain between from 1 to about 18 carbon atoms.
- Preferred mono-, di-and trialkyl phosphate esters, alkylaryl or arylalkyl phosphate esters are those prepared by reacting a C3-C18 aliphatic alcohol with phosphorous pentoxide. The phosphate intermediate interchanges its ester groups with triethylphosphate producing a more broad distribution of alkyl phosphate esters.
- the phosphate ester can be made by admixing with an alkyl diester, a mixture of low molecular weight alkyl alcohols or diols.
- the low molecular weight alkyl alcohols or diols preferably include C & to C10 alcohols or diols.
- triethanolamine are preferred.
- the corrosion inhibitor component can include a monomeric or oligomeric fatty acid.
- Preferred monomeric or oligomeric fatty acids are Ci 4 -C 2 2 saturated and unsaturated fatty acids as well as dimer, trimer and oligomer products obtained by polymerizing one or more of such fatty acids.
- the corrosion inhibitor component can comprise an alkoxylated amine.
- the alkoxylated amine can be an ethoxylated alkyl amine.
- the alkoxylated amine can be ethoxylated tallow amine.
- the alkoxylated amine can constitute 0 wt. % to 100 wt. %, about 10 to 60 wt. %, or about 20 to 30 wt.% of the corrosion inhibitor component, based on total weight of the corrosion inhibitor component.
- the corrosion inhibitor comprises the quaternary ammonium salt and the bis-quaternized compound of Formula (III).
- compositions disclosed herein can include a solvent.
- the solvent can be present in an amount of 5 wt. % to about 95 wt. %, about 20 wt. % to about 80 wt. %, or about 40 wt. % to about 60 wt. %, based on total weight of the composition.
- the solvent can constitute about 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90 or 95 wt. % of the composition.
- Suitable solvents include, but are not limited to, alcohols, hydrocarbons, ketones, ethers, alkylene glycols, glycol ethers, amides, nitriles, sulfoxides, esters, and water.
- the solvent can be water, isopropanol, methanol, ethanol, 2-ethylhexanol, heavy aromatic naphtha, toluene, ethylene glycol, ethylene glycol monobutyl ether (EGMBE), diethylene glycol monoethyl ether, or xylene.
- Representative polar solvents suitable for formulation with the composition include water, brine, seawater, alcohols (including straight chain or branched aliphatic such as methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, etc.), alkylene glycols (methylene glycol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, etc.) glycol ethers (diethyleneglycol monomethyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, etc.), ketones (cyclohexanone, diisobutylketone), ethers (diethyl ether, etc.), an alkylene carbonate (propylene carbonate, etc.), N-methylpyrrolidinone (NMP), ⁇ , ⁇ -dimethylformamide,
- non-polar solvents suitable for formulation with the composition include aliphatic hydrocarbons such as pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel, and the like; aromatic hydrocarbons such as toluene, xylene, heavy aromatic naphtha; and fatty acid derivatives (acids, esters, amides), and the like.
- the solvent can be a solvent compatible with an arctic environment, as for example, methanol, ethanol, ethylene glycol or glycerin, which improves the anti-freeze properties of the composition.
- Such solvent is typically present in an amount of about 5 to about 15 wt. %, and preferably about 10 wt. %, based on total weight of the composition to have an anti-freeze effect.
- compositions disclosed herein can include a sulfur-containing compound.
- the sulfur-containing compound can be present in an amount of about 1 wt. % to about 20 wt. %, about 1 wt. % to about 10 wt.%, or about 1 to about 5 wt. % based on total weight of the composition.
- the sulfur-containing compound can constitute about 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19 or 20 wt. % of the cleaner/corrosion inhibitor composition, based on total weight of the composition.
- Suitable sulfur-containing compounds include compounds that enhance the corrosion inhibiting and/or cleaning performance of the composition such as synergists.
- the sulfur-containing compound can include, but is not limited to, thioglycolic acid, 3,3'-dithiodipropionic acid, thiourea, 2-mercaptoethanol, L-cysteine, tert-butyl mercaptan, sodium thiosulfate, ammonium thiosulfate, sodium thiocyanate, ammonium thiocyanate, sodium metabisulfite, or a combination thereof.
- the sulfur-containing compound is 2-mercaptoethanol.
- compositions can optionally include one or more additives.
- Suitable additives include, but are not limited to, asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, hydrogen sulfide scavengers, gas hydrate inhibitors, biocides, pH modifiers, and surfactants.
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.1 to 5 wt. %, or from about 0.5 to 4 wt. % of an asphaltene inhibitor, based on total weight of the composition.
- Suitable asphaltene inhibitors include, but are not limited to, aliphatic sulfonic acids; alkyl aryl sulfonic acids; aryl sulfonates; lignosulfonates;
- alkylphenol/aldehyde resins and similar sulfonated resins polyolefin esters; polyolefin imides; polyolefin esters with alkyl, alkylenephenyl or alkylenepyridyl functional groups; polyolefin amides; polyolefin amides with alkyl, alkylenephenyl or alkylenepyridyl functional groups; polyolefin imides with alkyl, alkylenephenyl or alkylenepyridyl functional groups; alkenyl/vinyl pyrrolidone copolymers; graft polymers of polyolefins with maleic anhydride or vinyl imidazole; hyperbranched polyester amides;
- polyalkoxylated asphaltenes amphoteric fatty acids, salts of alkyl succinates, sorbitan monooleate, and polyisobutylene succinic anhydride.
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.1 to 5 wt. %, or from about 0.5 to 4 wt. % of a paraffin inhibitor, based on total weight of the composition.
- Suitable paraffin inhibitors include, but are not limited to, paraffin crystal modifiers, and dispersant/crystal modifier combinations.
- Suitable paraffin crystal modifiers include, but are not limited to, alkyl acrylate copolymers, alkyl acrylate vinylpyridine copolymers, ethylene vinyl acetate copolymers, maleic anhydride ester copolymers, branched polyethylenes, naphthalene, anthracene, microcrystalline wax and/or asphaltenes.
- Suitable dispersants include, but are not limited to, dodecyl benzene sulfonate, oxyalkylated alkylphenols, and oxyalkylated alkylphenolic resins.
- the composition can comprise from about 0.1 to 20 wt. %, from about 0.5 to 10 wt. %, or from about 1 to 10 wt. % of a scale inhibitor, based on total weight of the composition.
- Suitable scale inhibitors include, but are not limited to, phosphates, phosphate esters, phosphoric acids, phosphonates, phosphonic acids,
- polyacrylamides salts of acrylamidomethyl propane sulfonate/acrylic acid copolymer (AMPS/AA), phosphinated maleic copolymer (PHOS/MA), and salts of a polymaleic acid/acrylic acid/acrylamidomethyl propane sulfonate terpolymer (PMA/AA/AMPS).
- AMPS/AA acrylamidomethyl propane sulfonate/acrylic acid copolymer
- PHOS/MA phosphinated maleic copolymer
- PMA/AA/AMPS polymaleic acid/acrylic acid/acrylamidomethyl propane sulfonate terpolymer
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.5 to 5 wt. %, or from about 0.5 to 4 wt. % of an emulsifier, based on total weight of the composition.
- Suitable emulsifiers include, but are not limited to, salts of carboxylic acids, products of acylation reactions between carboxylic acids or carboxylic
- alkyl- saccharide emulsifiers anhydrides and amines, and alkyl, acyl and amide derivatives of saccharides (alkyl- saccharide emulsifiers).
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.5 to 5 wt. %, or from about 0.5 to 4 wt. % of a water clarifier, based on total weight of the composition.
- Suitable water clarifiers include, but are not limited to, inorganic metal salts such as alum, aluminum chloride, and aluminum chlorohydrate, or organic polymers such as acrylic acid based polymers, acrylamide based polymers,
- DMAC diallyldimethylammonium chloride
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.5 to 5 wt. %, or from about 0.5 to 4 wt. % of a dispersant, based on total weight of the composition.
- Suitable dispersants include, but are not limited to, aliphatic phosphonic acids with 2-50 carbons, such as hydroxyethyl diphosphonic acid, and aminoalkyl phosphonic acids, e.g. polyaminomethylene phosphonates with 2-10 N atoms e.g.
- each bearing at least one methylene phosphonic acid group examples of the latter are ethylenediamine tetra(methylene phosphonate), diethylenetriamine penta(methylene phosphonate), and the triamine- and tetramine-polymethylene phosphonates with 2-4 methylene groups between each N atom, at least 2 of the numbers of methylene groups in each phosphonate being different.
- suitable dispersion agents include lignin, or derivatives of lignin such as lignosulfonate and naphthalene sulfonic acid and derivatives.
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.5 to 5 wt. %, or from about 0.5 to 4 wt. % of an emulsion breaker, based on total weight of the composition.
- Suitable emulsion breakers include, but are not limited to,
- DBSA dodecylbenzylsulfonic acid
- NAXSA sodium salt of xylenesulfonic acid
- epoxylated and propoxylated compounds epoxylated and propoxylated compounds
- anionic cationic and nonionic surfactants and resins, such as phenolic and epoxide resins.
- the composition can comprise from about 0.5 to 20 wt. %, from about 1 to 15 wt. %, or from about 1 to 10 wt. % of an additional hydrogen sulfide scavenger, based on total weight of the composition.
- Suitable additional hydrogen sulfide scavengers include, but are not limited to, oxidants (e.g., inorganic peroxides such as sodium peroxide or chlorine dioxide); aldehydes (e.g., of 1 -10 carbons such as formaldehyde, glyoxal, glutaraldehyde, acrolein, or methacrolein; and triazines (e.g., monoethanolamine triazine, monomethylamine triazine, and triazines from multiple amines or mixtures thereof).
- oxidants e.g., inorganic peroxides such as sodium peroxide or chlorine dioxide
- aldehydes e.g., of 1 -10 carbons such as formaldehyde, glyoxal, glutaraldehyde, acrolein, or methacrolein
- triazines e.g., monoethanolamine triazine, monomethylamine triazine
- the composition can comprise from about 0.1 to 25 wt. %, from about 0.5 to 20 wt. %, or from about 1 to 10 wt. % of a gas hydrate inhibitor, based on total weight of the composition.
- Suitable gas hydrate inhibitors include, but are not limited to, thermodynamic hydrate inhibitors (THI), kinetic hydrate inhibitors (KHI), and anti- agglomerates (AA).
- Suitable thermodynamic hydrate inhibitors include, but are not limited to, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, sodium bromide, formate brines (e.g.
- polyols such as glucose, sucrose, fructose, maltose, lactose, gluconate, monoethylene glycol, diethylene glycol, triethylene glycol, mono-propylene glycol, dipropylene glycol, tripropylene glycols, tetrapropylene glycol, monobutylene glycol, dibutylene glycol, tributylene glycol, glycerol, diglycerol, triglycerol, and sugar alcohols (e.g. sorbitol, mannitol)), methanol, propanol, ethanol, glycol ethers (such as diethyleneglycol monomethylether,
- composition can comprise from about 0.1 to 25 wt. %, from about 0.5 to 20 wt. %, or from about 1 to 10 wt. % of a kinetic hydrate inhibitor or anti- agglomerate, based on total weight of the composition.
- Suitable kinetic hydrate inhibitors and anti-agglomerates include, but are not limited to, polymers and
- copolymers such as hydroxyethylcellulose (HEC)
- polysaccharides such as hydroxyethylcellulose (HEC)
- carboxymethylcellulose CMC
- lactams such as polyvinylcaprolactam, polyvinyl lactam
- pyrrolidones such as polyvinyl pyrrolidone of various molecular weights
- surfactants such as fatty acid salts, ethoxylated alcohols, propoxylated alcohols, sorbitan esters, ethoxylated sorbitan esters, polyglycerol esters of fatty acids, alkyl glucosides, alkyl polyglucosides, alkyl sulfates, alkyl sulfonates, alkyl ester sulfonates, alkyl aromatic sulfonates, alkyl betaine, alkyl amido betaines), hydrocarbon based dispersants (such as lignosulfonates,
- iminodisuccinates polyaspartates
- amino acids amino acids
- proteins proteins
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.5 to 5 wt. %, or from about 0.5 to 4 wt. % of a biocide, based on total weight of the composition.
- Suitable biocides include, but are not limited to, oxidizing and non- oxidizing biocides.
- Suitable non-oxidizing biocides include, for example, aldehydes (e.g., formaldehyde, glutaraldehyde, and acrolein), amine-type compounds (e.g., quaternary amine compounds and cocodiamine), halogenated compounds (e.g., 2- bromo-2-nitropropane-3-diol (Bronopol) and 2-2-dibromo-3-nitrilopropionamide
- aldehydes e.g., formaldehyde, glutaraldehyde, and acrolein
- amine-type compounds e.g., quaternary amine compounds and cocodiamine
- halogenated compounds e.g., 2- bromo-2-nitropropane-3-diol (Bronopol) and 2-2-dibromo-3-nitrilopropionamide
- Suitable oxidizing biocides include, for example, sodium hypochlorite, trichloroisocyanuric acids, dichloroisocyanuric acid, calcium hypochlorite, lithium hypochlorite, chlorinated hydantoins, stabilized sodium hypobromite, activated sodium bromide, brominated hydantoins, chlorine dioxide, ozone, and peroxides.
- the composition can comprise from about 0.1 to 20 wt. %, from about 0.5 to 10 wt. %, or from about 0.5 to 5 wt. % of a pH modifier, based on total weight of the composition.
- Suitable pH modifiers include, but are not limited to, alkali hydroxides, alkali carbonates, alkali bicarbonates, alkaline earth metal hydroxides, alkaline earth metal carbonates, alkaline earth metal bicarbonates and mixtures or combinations thereof.
- Exemplary pH modifiers include sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium oxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, magnesium oxide, and magnesium hydroxide.
- the composition can comprise from about 0.1 to 10 wt. %, from about 0.5 to 5 wt. %, or from about 0.5 to 4 wt. % of a surfactant, based on total weight of the composition.
- Suitable surfactants include, but are not limited to, anionic surfactants and nonionic surfactants.
- Anionic surfactants include alkyl aryl sulfonates, olefin sulfonates, paraffin sulfonates, alcohol sulfates, alcohol ether sulfates, alkyl
- Nonionic surfactants include alcohol alkoxylates, alkylphenol alkoxylates, block copolymers of ethylene, propylene and butylene oxides, alkyl dimethyl amine oxides, alkyl-bis(2- hydroxyethyl) amine oxides, alkyl amidopropyl dimethyl amine oxides,
- alkylamidopropyl-bis(2-hydroxyethyl) amine oxides alkyl polyglucosides
- polyalkoxylated glycerides polyalkoxylated glycerides, sorbitan esters and polyalkoxylated sorbitan esters, and alkoxyl polyethylene glycol esters and diesters.
- betaines and sultanes amphoteric surfactants such as alkyl amphoacetates and amphodiacetates, alkyl amphopropionates and amphodipropionates, and alkyliminodipropionate.
- the surfactant can be a quaternary ammonium compound, an amine oxide, an ionic or nonionic surfactant, or any combination thereof.
- Suitable quaternary amine compounds include, but are not limited to, alkyl benzyl ammonium chloride, benzyl cocoalkyl(Ci 2 -Ci 8 )dimethylammonium chloride, dicocoalkyl (C 12 - Ci 8 )dimethylammonium chloride, ditallow dimethylammonium chloride, di(hydrogenated tallow alkyl)dimethyl quaternary ammonium methyl chloride, methyl bis(2-hydroxyethyl cocoalkyl(Ci 2 -Ci8) quaternary ammonium chloride, dimethyl(2-ethyl) tallow ammonium methyl sulfate, n-dodecylbenzyldimethylammonium chloride, n-octadecylbenzyld
- alkyltrimethylammonium chloride and hydrogenated tallow alkyl (2-ethylhexyl) dimethyl quaternary ammonium methyl sulfate.
- compositions made according to the invention can further include additional functional agents or additives that provide a beneficial property.
- additional functional agents or additives that provide a beneficial property.
- the amount of an additional agent or additive, when present, will vary according to the particular composition being manufactured and its intended use as one skilled in the art will appreciate.
- compositions of the invention can be prepared by combining the iron sulfide dissolver with a solvent to form a solution. To the solution can be added one or more additional corrosion inhibitors, sulfur-containing compounds, and/or solvents, and any other additives.
- compositions of the invention can be used for inhibiting corrosion and/or removing hydrocarbonaceous deposits (e.g., schmoo) in oil and gas
- compositions of the invention can be used in any industry where it is desirable to inhibit corrosion and/or remove hydrocarbonaceous deposits from a surface.
- the method comprises contacting any of the compositions described herein or the iron sulfide dissolver with the metal surface to reduce, inhibit or prevent corrosion and/or remove hydrocarbonaceous deposits from the metal surface.
- compositions can be used for inhibiting corrosion and/or removing hydrocarbonaceous deposits by treating a gas or liquid stream with an effective amount of a composition of the invention, as described herein.
- the cleaner/corrosion inhibitor compositions can be used in water systems, condensate/oil systems/gas systems, or any combination thereof.
- the compositions can be used in controlling scale on heat exchanger surfaces.
- compositions can be applied to a gas or liquid produced, or used in the production, transportation, storage, and/or separation of crude oil or natural gas.
- compositions can be applied to a gas stream used or produced in a coal-fired process, such as a coal-fired power plant.
- compositions can be applied to a gas or liquid produced or used in a waste-water process, a farm, a slaughter house, a land-fill, a municipality waste-water plant, a coking coal process, or a biofuel process.
- a fluid to which the compounds and compositions can be introduced can be an aqueous medium.
- the aqueous medium can comprise water, gas, and optionally liquid hydrocarbon.
- a fluid to which the compounds and compositions can be introduced can be a liquid hydrocarbon.
- the liquid hydrocarbon can be any type of liquid hydrocarbon including, but not limited to, crude oil, heavy oil, processed residual oil, bituminous oil, coker oils, coker gas oils, fluid catalytic cracker feeds, gas oil, naphtha, fluid catalytic cracking slurry, diesel fuel, fuel oil, jet fuel, gasoline, and kerosene.
- the fluid or gas can be a refined hydrocarbon product.
- a fluid or gas treated with a composition of the invention can be at any selected temperature, such as ambient temperature or an elevated temperature.
- the fluid (e.g., liquid hydrocarbon) or gas can be at a temperature of from about 40 °C to about 250 °C.
- the fluid or gas can be at a temperature of from -50 °C to 300 °C, 0 °C to 200 °C, 10 °C to 100 °C, or 20 °C to 90 °C.
- the fluid or gas can be at a temperature of -20 °C, -15 °C, -10 °C, -5 °C, or 0 °C.
- the fluid or gas can be found in an arctic environment, and can have a temperature and salinity typical of such environment.
- compositions of the invention can be added to a fluid at various levels of water cut.
- the water cut can be from 0% to 100% volume/volume (v/v), from 1 % to 80% v/v, or from 1 % to 60% v/v.
- the fluid can be an aqueous medium that contains various levels of salinity.
- the fluid can have a salinity of 0% to 25%, about 1 % to 24%, or about 10% to 25% weight/weight (w/w) total dissolved solids (TDS).
- the fluid or gas in which the compositions of the invention are introduced can be contained in and/or exposed to many different types of apparatuses.
- the fluid or gas can be contained in an apparatus that transports fluid or gas from one point to another, such as an oil and/or gas pipeline.
- the apparatus can be part of an oil and/or gas refinery, such as a pipeline, a separation vessel, a dehydration unit, or a gas line.
- the compositions can be introduced to large diameter flow lines of from about 1 inch to about 4 feet in diameter, small gathering lines, small flow lines and headers.
- the fluid can be contained in and/or exposed to an apparatus used in oil extraction and/or production, such as a wellhead.
- the apparatus can be part of a coal- fired power plant.
- the apparatus can be a scrubber (e.g., a wet flue gas desulfurizer, a spray dry absorber, a dry sorbent injector, a spray tower, a contact or bubble tower, or the like).
- the apparatus can be a cargo vessel, a storage vessel, a holding tank, or a pipeline connecting the tanks, vessels, or processing units.
- the surface can be a metal surface, such as carbon steel conduit or pipeline or mild steel conduit or pipeline.
- compositions of the invention can be introduced into a fluid or gas by any appropriate method for ensuring dispersal through the fluid or gas.
- composition can be added to the hydrocarbon fluid before the hydrocarbon fluid contacts the surface.
- composition can be added at a point in a flow line upstream from the point at which corrosion prevention and/or schmoo removal is desired.
- compositions can be injected using mechanical equipment such as chemical injection pumps, piping tees, injection fittings, atomizers, quills, and the like.
- compositions of the invention can be introduced with or without one or more additional polar or non-polar solvents depending upon the application and requirements.
- compositions of the invention can be pumped into an oil and/or gas pipeline using an umbilical line.
- a capillary injection system can be used to deliver the compositions to a selected fluid.
- a fluid to which the compositions can be introduced can be an aqueous medium.
- the aqueous medium can comprise water, gas, and optionally liquid hydrocarbon.
- a fluid to which the compositions can be introduced can be a liquid hydrocarbon.
- compositions can be introduced into a liquid and mixed.
- compositions can be injected into a gas stream as an aqueous or non-aqueous solution, mixture, or slurry.
- the fluid or gas can be passed through an absorption tower comprising a composition of the invention.
- compositions can be applied to a fluid or gas to provide any selected concentration.
- the compositions of the invention are typically added to a flow line to provide an effective treating dose of the described compositions from about 0.01 to about 5,000 ppm.
- the compositions can be applied to a fluid or gas to provide at a concentration of about 1 parts per million (ppm) to about 1 ,000,000 ppm, about 1 parts per million (ppm) to about 100,000 ppm, or about 10 ppm to about 75,000 ppm.
- the compositions can be applied to a fluid at a concentration of about 100 ppm to about 10,000 ppm, about 200 ppm to about 8,000 ppm, or about 500 ppm to about 6,000 ppm.
- the compositions can be applied to a fluid or gas to provide a
- Each system can have its own requirements, and the effective amount of a composition to sufficiently reduce the rate of corrosion and/or remove schmoo can vary with the system in which it is used.
- compositions can be applied continuously, in batch, or a combination thereof.
- the composition doses can be continuous to prevent corrosion or intermittent (i.e., batch treatment) to remove hydrocarbonaceous deposits.
- the composition doses can be continuous/ maintained and/or intermittent to both inhibit corrosion and remove deposits.
- Dosage rates for continuous treatments typically range from about 10 to about 500 ppm, or about 10 to about 200 ppm.
- Dosage rates for batch treatments typically range from about 10 to about 400,000 ppm, or about 10 to about 20,000 ppm.
- the composition can also be applied as a pill to a pipeline, for example, to provide a high dose (e.g., 20,000 ppm) of the composition.
- the flow rate of a flow line in which the composition is used can be between 0 and 100 feet per second, or between 0.1 and 50 feet per second.
- the compositions can be formulated with water in order to facilitate addition to the flow line.
- suitable substituent is intended to mean a chemically acceptable functional group, preferably a moiety that does not negate the activity of the inventive compounds.
- suitable substituents include, but are not limited to halo groups, perfluoroalkyl groups, perfluoroalkoxy groups, alkyl groups, alkenyl groups, alkynyl groups, hydroxy groups, oxo groups, mercapto groups, alkylthio groups, alkoxy groups, aryl or heteroaryl groups, aryloxy or heteroaryloxy groups, arylalkyl or heteroarylalkyl groups, arylalkoxy or heteroarylalkoxy groups, carboxyl groups, heterocyclic groups, cycloalkyl groups, amino groups, alkyl- and dialkylamino groups, carbamoyl groups, alkylcarbonyl groups, alkoxycarbonyl groups,
- alkylaminocarbonyl groups dialkylamino carbonyl groups, arylcarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, and arylsulfonyl groups.
- substituents can be substituted by additional substituents.
- alkyl refers to a linear or branched
- hydrocarbon radical preferably having 1 to 32 carbon atoms (i.e., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 39, 30, 31 , or 32 carbons).
- Alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, secondary-butyl, and tertiary-butyl. Alkyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
- alkenyl refers to a straight or branched hydrocarbon radical, preferably having 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 39, 30, 31 , or 32 carbons, and having one or more carbon-carbon double bonds.
- Alkenyl groups include, but are not limited to, ethenyl, 1 -propenyl, 2-propenyl (allyl), isopropenyl, 2-methyl-1 -propenyl, 1 -butenyl, and 2-butenyl. Alkenyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
- alkynyl refers to a straight or branched hydrocarbon radical, preferably having 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 39, 30, 31 , or 32 carbons, and having one or more carbon-carbon triple bonds.
- Alkynyl groups include, but are not limited to, ethynyl, propynyl, and butynyl. Alkynyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
- alkoxy refers to an alkyl group, as defined herein, appended to the parent molecular moiety through an oxygen atom.
- aryl means monocyclic, bicyclic, or tricyclic aromatic radicals such as phenyl, naphthyl, tetrahydronaphthyl, indanyl and the like; optionally substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
- Alkoxycarbonylamino refers to an alkyl carbamate group.
- Alkylcarbonylamino refers to groups such as acetamide.
- cycloalkyl refers to a mono, bicyclic or tricyclic carbocyclic radical (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclopentenyl, cyclohexane, bicyclo[2.2.1 ]heptanyl, bicyclo[3.2.1 ]octanyl and bicyclo[5.2.0]nonanyl, etc.); optionally containing 1 or 2 double bonds. Cycloalkyl groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
- alkylene denotes a bivalent alkyl group such as methylene (-CH 2 -) or ethylene (-CH 2 CH 2 -).
- alkylene denotes an optionally
- halo or halogen
- halogen refers to a fluoro, chloro, bromo or iodo radical.
- halide refers to fluoride, chloride, bromide, iodide or the like.
- heteroaryl refers to a monocyclic, bicyclic, or tricyclic aromatic heterocyclic group containing one or more heteroatoms selected from 0, S and N in the ring(s).
- Heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, furyl, imidazolyl, pyrrolyl, oxazolyl (e.g., 1 ,3- oxazolyl, 1 ,2-oxazolyl), thiazolyl (e.g., 1 ,2-thiazolyl, 1 ,3-thiazolyl), pyrazolyl, tetrazolyl, triazolyl (e.g., 1 ,2,3-triazolyl, 1 ,2,4-triazolyl), oxadiazolyl (e.g., 1 ,2,3-
- Heteroaryl groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
- the term "heterocycle,” as used herein, refers to a monocyclic, bicyclic, or tricyclic group containing 1 to 4 heteroatoms selected from N, 0, S(0) n , P(0) n , P X , NH or NR X , wherein R x is a suitable substituent.
- Heterocyclic groups optionally contain 1 or 2 double bonds.
- Heterocyclic groups include, but are not limited to, azetidinyl, tetrahydrofuranyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl, tetrahydrothiazinyl, tetrahydrothiadiazinyl, morpholinyl, oxetanyl, tetrahydrodiazinyl, oxazinyl, oxathiazinyl, indolinyl, isoindolinyl, quinuclidinyl, chromanyl, isochromanyl, and benzoxazinyl.
- Examples of monocyclic saturated or partially saturated ring systems are tetrahydrofuran-2-yl, tetrahydrofuran-3- yl, imidazolidin-1 -yl, imidazolidin-2-yl, imidazolidin-4-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1 -yl, piperidin-2-yl, piperidin-3-yl, piperazin-1 -yl, piperazin-2-yl, piperazin-3-yl, 1 ,3-oxazolidin-3-yl, isothiazolidine, 1 ,3-thiazolidin-3-yl, 1 ,2-pyrazolidin-2- yl, 1 ,3-pyrazolidin-1 -yl, thiomorpholin-yl, 1 ,2-tetrahydrothiazin-2-yl, 1 ,3- tetrahydro
- hydroxy refers to an -OH group.
- counterion means a halide (e.g., fluoride, chloride, bromide, iodide), a carboxylate anion, such as selected from deprotonation of mineral acid, acrylic acid, acetic acid, methacrylic acid, glycolic acid, thioglycolic acid, propionic acid, butyric acid, and the like, or any other anionic constituent that satisfies the charge balance necessary to form a neutral molecule.
- halide e.g., fluoride, chloride, bromide, iodide
- carboxylate anion such as selected from deprotonation of mineral acid, acrylic acid, acetic acid, methacrylic acid, glycolic acid, thioglycolic acid, propionic acid, butyric acid, and the like, or any other anionic constituent that satisfies the charge balance necessary to form a neutral molecule.
- sweetening can refer to a process that removes sulfur species from a gas or liquid.
- the sulfur species can include hydrogen sulfide and mercaptans.
- hydrocarbonaceous deposit refers to any deposit including at least one hydrocarbon constituent and forming on the inner surface of flowlines, pipelines, injection lines, wellbore surfaces, storage tanks, process equipment, vessels, the like, and other components in oil and gas applications. Such deposits also include “schmoo,” which refers to a solid, paste-like, or sludge-like substance that adheres to almost any surface with which it comes in contact and is particularly difficult to remove. Deposits contributing to schmoo can include, for example, sand, clays, sulfur, naphthenic acid salts, corrosion byproducts, biomass, and other hydrocarbonaceous materials bound together with oil. These terms are used interchangeably herein.
- TOFA refers to a tall oil fatty acid that is a distilled product derived from trees and includes a mixture of fatty acids.
- Table 1 summarizes exemplary compositions of the invention.
- the raw materials are commercially available.
- compositions of Table 1 can be prepared by adding sodium gluconate to distilled water to form a solution.
- a mixture of benzyl dimethyl C12-C18 alkyl ammonium chloride, a bis-quaternized compound and 2-mercaptoethanol can be combined with the solution, and then another solvent can be added with shaking to form the composition.
- the compositions can be visually inspected after a three week period to determine whether any precipitation, flocculation or phase separation occurred at room temperature.
- the effect of different solvents was tested in Examples 6 to 1 1 . Each of these examples was prepared with the same amount of iron sulfide dissolver, solvent and corrosion inhibitor/sulfur-containing compound, but the solvent species were varied. The variation in solvents did not impact the stability of the formulation, and the observations are reported in Table 1 .
- R T is derived from a mixture of tall oil fatty acids and is predominantly a mixture
- the counter and reference electrodes were both 1018 carbon steel. The electrodes were all cleaned and polished prior to testing. Data were collected for four hours before each of the compositions was dosed into its respective cell. Data were collected overnight.
- the synthetic brine was composed of 5.64 g CaCI 2 '2H 2 0, 7.2 g MgCI 2 '6H 2 0, 1 .32 g KCI, 0.96 g Na 2 S0 4 , 16.8 g NaHC0 3 , 205.8 g. NaCI, 1 .08 g NaBr, and 10.8 g acetic acid in 12 liters of water.
- the brine had a pH of 5.5
- Aqueous samples held at 150 °F were prepared using iron chloride and sodium sulfide to afford an aqueous iron sulfide composition having about 30 ppm iron present.
- the experimental treatments of a commercially available corrosion inhibitor formulation, a sample of the corrosion inhibitor formulation spiked with 25% THPS, and another sample of the corrosion inhibitor formulation spiked with 25% sodium gluconate were then added to the aqueous samples which were subsequently held for another 30 minutes.
- the samples were then filtered using a 0.2 micron filter and the supernatant analyzed for iron by inductively coupled plasma analysis.
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Abstract
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Priority Applications (5)
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EP17817551.9A EP3548581B1 (en) | 2016-11-30 | 2017-11-30 | Composition for remediating iron sulfide in oilfield production systems |
CA3045314A CA3045314A1 (en) | 2016-11-30 | 2017-11-30 | Composition for remediating iron sulfide in oilfield production systems |
EP23194956.1A EP4296403A3 (en) | 2016-11-30 | 2017-11-30 | Composition for remediating iron sulfide in oilfield production systems |
BR112019011040A BR112019011040A2 (en) | 2016-11-30 | 2017-11-30 | composition, method of inhibition, and use of the composition. |
MX2019006279A MX2019006279A (en) | 2016-11-30 | 2017-11-30 | Composition for remediating iron sulfide in oilfield production systems. |
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US201662428123P | 2016-11-30 | 2016-11-30 | |
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US (2) | US11597868B2 (en) |
EP (2) | EP4296403A3 (en) |
BR (1) | BR112019011040A2 (en) |
CA (1) | CA3045314A1 (en) |
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MX2019006279A (en) | 2019-08-21 |
US11597868B2 (en) | 2023-03-07 |
US20230183554A1 (en) | 2023-06-15 |
EP3548581B1 (en) | 2023-09-06 |
EP4296403A2 (en) | 2023-12-27 |
CA3045314A1 (en) | 2018-06-07 |
EP4296403A3 (en) | 2024-02-28 |
US20180148632A1 (en) | 2018-05-31 |
BR112019011040A2 (en) | 2019-10-08 |
EP3548581A1 (en) | 2019-10-09 |
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